Chlormezanone

"Trancopal" redirects here. For Trancopal Dolo, see Flupirtine.

Chlormezanone

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	M03BB02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	40.5 hours
Identifiers
IUPAC name 2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
CAS Number	80-77-3^Y
PubChem CID	2717
IUPHAR/BPS	7323
DrugBank	DB01178^Y
ChemSpider	2616^Y
UNII	GP568V9G19
KEGG	D00268^Y
ChEBI	CHEBI:3619^Y
ChEMBL	ChEMBL1200714^N
CompTox Dashboard (EPA)	DTXSID3022798
ECHA InfoCard	100.001.190
Chemical and physical data
Formula	C11H12ClNO3S
Molar mass	273.73 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=S1(CCC(N(C)C1C2=CC=C(C=C2)Cl)=O)=O
InChI InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3^Y Key:WEQAYVWKMWHEJO-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

Chlormezanone (marketed under the brandname Trancopal or Fenaprim) is a drug used as an anxiolytic and a muscle relaxant.^[1]

Its use was discontinued in many countries in 1996 due to rare but serious cases of toxic epidermal necrolysis.^[2]

Synthesis

Chlormezanone synthesis^[3][4]

References

1. Turner P, Volan G, Wiseman H (1997). Drugs Handbook. UK: Palgrave Macmillan. p. 20. ISBN 978-1-349-13937-8.
2. Lerch M, Mainetti C, Terziroli Beretta-Piccoli B, Harr T (February 2018). "Current Perspectives on Stevens-Johnson Syndrome and Toxic Epidermal Necrolysis". Clinical Reviews in Allergy & Immunology. 54 (1): 147–176. doi:10.1007/s12016-017-8654-z. PMID 29188475. S2CID 46796285.
3. US 3082209, Surrey AR, "4-metathiazanone derivatives and their preparation", issued 1958, assigned to Sterling Drug Inc. 
4. Surrey AR, Webb WG, Gesler RM (1958). "Central Nervous System Depressants. The Preparation of Some 2-Aryl-4-metathiazanones". Journal of the American Chemical Society. 80 (13): 3469–3471. doi:10.1021/ja01546a065.

Further reading

• Wollina U, Hipler UC, Seeling A, Oelschlager H (2005). "Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro". Skin Pharmacology and Physiology. 18 (3): 132–138. doi:10.1159/000084910. PMID 15897685. S2CID 36642315.
• Seeling A, Oelschläger H, Rothley D (April 2000). "[Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone]". Die Pharmazie. 55 (4): 293–296. PMID 10798243.
• Oelschläger H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, et al. (September 1998). "[Cleavage and biotransformation of the central muscle relaxant chlormezanone]". Die Pharmazie. 53 (9): 620–624. PMID 9770210.
• Gautier V, Vinçon G, Demotes-Mainard F, Albin H (1990). "[Pharmacokinetics of chlormezanone in healthy volunteers]". Therapie. 45 (4): 315–319. PMID 2399514.